(1S,2R)-(3-azido-1-benzyl-2-hydroxy-propyl)-carbamic acid t-butyl ester → tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate

HRID 336473Notes

Reaction equation

HRID 336473 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:9]([OH:14])[CH2:10][N:11]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C@H:9]([OH:14])[CH2:10][NH2:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11722693(1S,2R)-(3-azido-1-benzyl-2-hydroxy-propyl)-carbamic acid t-butyl ester

Product 1

HCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1S,2R)-(3-azido-1-benzyl-2-hydroxy-propyl)-carbamic acid t-butyl ester (2.5 g, 8.17 mmol) prepared in Step A was dissolved in methanol (15 mL), to which was added Pd/C (100 mg). The mixture was reacted for 12 h in a hydrogen reactor (50 psi), and filtered through a cellite. The solvent was removed under reduced pressure, and the residue was used in the next reaction without further purification.

Workup

  1. customThe mixture was reacted for 12 h in a hydrogen reactor (50 psi)
  2. filtrationfiltered through a cellite
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was used in the next reaction without further purification

Sources & evidence

ORD record
ord-64dd160a83b44f74b1bd5e4687c29288
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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